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Acid catalyzed ring closure reactions of electrophilic alkenes |
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| Authors: | Roland Verh , Norbert de Kimpe, Dirk Courtheyn, Laurent de Buyck,Niceas Schamp |
| Affiliation: | State University of Gent, Faculty of Agricultural Sciences, Laboratory of Organic Chemistry, Coupure Links 653, B-9000 Gent, Belgium |
| Abstract: | Treatment of -acyl-,β-unsaturated ketones with sulfuric acid or dimethylformamide-hydrogen chloride or p-toluenesulfonic acid gave rise to 3-acyl-2-alkyl-4,5-dihydrofurans. Similar cyclization of -acyl-,β-unsaturated esters initially afforded 3-alkoxycarbonyl-2-alkyl-4,5-dihydrofurans which were transformed into 2-acylbutanolides on further reaction with sulfuric acid. This acid catalyzed cyclization is strongly dependent upon the substitution pattern of the electrophilic alkenes, the acid used and reaction conditions. |
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